1,4-Diphenyl-4,5-dihydro-1H-1,4-epoxido-benzo[d][1,2]dioxepin | 91859-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,4-Diphenyl-4,5-dihydro-1H-1,4-epoxido-benzo[d][1,2]dioxepin
• 英文别名: 4,5-dihydro-1,4-diphenyl-1,4-epoxy-1H-2,3-benzodioxepin；1,9-Diphenyl-10,11,12-trioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
• CAS: 91859-82-4
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: ZJRFXAUNUZCKTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Diphenyl-4,5-dihydro-1H-1,4-epoxido-benzo[d][1,2]dioxepin 在 palladium(II) oxide 、 calcium carbonate 作用下， 生成 2-(2-benzoylphenyl)-1-phenylethanone
  参考文献：
  名称：

  Bailey, Chemische Berichte, 1954, vol. 87, p. 993,995 Anm. 3

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-Epoxy-2,3-diphenylindan 在 联苯 、 9,10-二氰基蒽 、 氧气 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85%的产率得到1,4-Diphenyl-4,5-dihydro-1H-1,4-epoxido-benzo[d][1,2]dioxepin
  参考文献：
  名称：

  通过环氧化物的电子转移光氧化来光化学制备臭氧化物

  摘要：

  9,10-二氰基蒽（DCA）使在氧饱和的乙腈中的环氧化物的电子转移光氧合反应敏感，从而形成臭氧化物。与SCE相比，氧化电位低于2 V的环氧化合物会猝灭DCA的荧光，仅通过DCA即可将其转化为臭氧化物。在这些条件下，不会淬灭DCA的单重激发态的环氧化合物不会发生反应。然而，这些环氧化物的光氧化可以通过添加联苯（BP）作为催化剂或共敏化剂来实现。对顺式-和反式-2,3-二芳基环氧乙烷的反应的立体化学研究表明，两种同分异构的环氧化物都只转化为相应的顺式-臭氧化物。顺式和-的共同增感光氧合反式-2,3-二苯基环氧乙烷仅提供顺式-3,5-二苯基-1,2,4-三氧戊环。对于不需要BP共敏化的更容易氧化的2,3-二萘并氧杂蒽的电子转移光氧化，遵循相同的立体化学过程。萘基取代的臭氧化物的立体化学已经明确地由顺式-3,5-双（2'-萘基）-1,2,4-三氧戊环的X射线结构确定。通过顺式臭氧化制备相应的反式-臭氧化物-1

  DOI：

  10.1016/s0040-4020(01)96597-4

文献信息

• Ozonide compounds with inhibitory activity for urokinase production and angiogenesis
  申请人：Taiho Pharmaceutical Company Ltd.

  公开号：US06365610B1

  公开（公告）日：2002-04-02

  The invention provides a urokinase production inhibitor or angiogenesis inhibitor comprising as an active component an ozonide derivative represented by the formula (1), and method of prevention or therapy using the inhibitor wherein A is an oxygen atom or N—R (wherein R is phenyl or phenyl having as a substituent lower alkyl having 1 to 6 carbon atoms, lower alkoxyl having 1 to 6 carbon atoms or a halogen atom); B is an oxo group or —R4; and (1) when A is an oxygen atom, R1 is a hydrogen atom, etc., R2 is phenyl, etc., R3 is a hydrogen atom, etc., B is an oxo group or —R4, R4 is a hydrogen atom, etc., R5 is a hydrogen atom, etc.; (2) when A is N—R, R1 is a hydrogen atom, etc., R2 is a hydrogen atom, etc., R3 is a hydrogen atom, etc., B is —R4, R4 is a hydrogen atom, etc., R5 is a hydrogen atom, etc.

  该发明提供了一种尿激酶产生抑制剂或血管生成抑制剂，其包括作为活性成分的一种由式（1）表示的臭氧化物衍生物，以及使用该抑制剂的预防或治疗方法，其中A是氧原子或N—R（其中R是苯基或苯基，其取代基为1至6个碳原子的较低烷基，1至6个碳原子的较低烷氧基或卤原子）；B是羰基或—R4；当A是氧原子时，R1是氢原子等，R2是苯基等，R3是氢原子等，B是羰基或—R4，R4是氢原子等，R5是氢原子等；当A是N—R时，R1是氢原子等，R2是氢原子等，R3是氢原子等，B是—R4，R4是氢原子等，R5是氢原子等。
• UROKINASE PRODUCTION INHIBITORS, ANGIOGENESIS INHIBITORS AND METHODS OF PREVENTION OR TREATMENT WITH BOTH
  申请人：TAIHO PHARMACEUTICAL COMPANY LIMITED

  公开号：EP1033130A1

  公开（公告）日：2000-09-06

  The invention provides a urokinase production inhibitor or angiogenesis inhibitor comprising as an active component an ozonide derivative represented by the formula (1), and method of prevention or therapy using the inhibitor wherein A is an oxygen atom or N-R (wherein R is phenyl or phenyl having as a substituent lower alkyl having 1 to 6 carbon atoms, lower alkoxyl having 1 to 6 carbon atoms or a halogen atom); B is an oxo group or -R4; and (1) when A is an oxygen atom, R1 is a hydrogen atom, etc., R2 is phenyl, etc., R3 is a hydrogen atom, etc., B is an oxo group or -R4, R4 is a hydrogen atom, etc., R5 is a hydrogen atom, etc.; (2) when A is N-R, R1 is a hydrogen atom, etc., R2 is a hydrogen atom, etc., R3 is a hydrogen atom, etc., B is -R4, R4 is a hydrogen atom, etc., R5 is a hydrogen atom, etc.

  本发明提供了一种尿激酶生成抑制剂或血管生成抑制剂，其活性成分包括由式(1)表示的臭氧衍生物，以及使用该抑制剂进行预防或治疗的方法 其中 A 是氧原子或 N-R(其中 R 是苯基或具有 1 至 6 个碳原子的低级烷基、具有 1 至 6 个碳原子的低级烷氧基或卤原子作为取代基的苯基)；B 是氧代基团或 -R4；以及 (1) 当 A 是氧原子时，R1 是氢原子等，R2 是苯基等、R3 是氢原子等，B 是氧代基团或-R4，R4 是氢原子等，R5 是氢原子等；(2) 当 A 是 N-R，R1 是氢原子等，R2 是氢原子等，R3 是氢原子等，B 是-R4，R4 是氢原子等，R5 是氢原子等。
• Ozonolysis of vinyl ethers. Evidence for intramolecular oxygen transfer from a carbonyl oxide moiety to a methoxyvinyl group
  作者：Norinaga Nakamura、Masatomo Nojima、Shigekazu Kusabayashi

  DOI：10.1021/ja00250a034

  日期：1987.8
• Ozonolyses of 1,2-diphenyl- and 2-phenylindene
  作者：Toshiya Sugimoto、Koichi Teshima、Norinaga Nakamura、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00053a026

  日期：1993.1

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.
• Formation of the crossed product 1,4-disubstituted 2,3,5,6,11-pentaoxabicyclo[5.3.1]undecane from a mixture of two kinds of ozonides in the presence of an acid catalyst. Elucidation of the intermediates in the acidolysis of an ozonide
  作者：Masahiro Miura、Masatomo Nojima、Shigekazu Kusabayashi、Shigeru Nagase

  DOI：10.1021/ja00397a034

  日期：1981.4